Dicyclohexylcarbodiimide → L-Isoleucine

HRID 2293402Notes

Reaction equation

HRID 2293402 reaction equation
C(CN1CCC[C@H]1C(N(CC1C=CC=CC=1)[C:10](=[O:17])[C@H:11]([C@H:13]([CH2:15][CH3:16])[CH3:14])[NH2:12])=O)(O)=O.C1(N=C=NC2CCCCC2)CCCCC1.CC(C)=CCC/C(/C)=C/CC/C(/C)=C/C[OH:55]>ClCCl>[NH2:12][C@H:11]([C:10]([OH:17])=[O:55])[C@H:13]([CH2:15][CH3:16])[CH3:14]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 445070FarnesolHCID 131720284L-isoleucine, N-[1-(carboxymethyl)-L-prolyl] benzylamide

Product 1

HCID 6306L-IsoleucineYield 114.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of L-isoleucine, N-[1-(carboxymethyl)-L-prolyl] benzylamide (67 mg, 0.18 mmol), 4-N,N-dimethylaminopyridine (6.1 mg, 0.05 mmol, 0.3 eq), 1,3-dicyclohexylcarbodiimide (64 mg, 0.31 mmol, 1.8 eq) in dichloromethane (2.0 mL) was treated with trans,trans farnesol (55 uL, 0.22 mmol, 1.2 eq). After TLC indicated the reaction was complete, the mixture was purified by HPLC to provide 27 mg (26%) of L-isoleucine, N-[1-(2-[1-(3,7,11-trimethyldodeca-2,6,10-trien-1-ol)]-2-oxoethyl)-L-proline] benzylamide.

Workup

  1. customthe mixture was purified by HPLC

Sources & evidence

ORD record
ord-be5989ac63444d0b82f64c87545c25a9
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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